He was drafted in the first round of the Ontario Hockey League (OHL) priority selection by the Owen Sound Attack in May 2005.

[6] However, at the end of the season Bailey suffered facial fractures after being boarded by Alexei Ponikarovsky of the Pittsburgh Penguins.

[9] Upon returning, he had no points in a 13-game stretch, prompting the Islanders to send Bailey to their American Hockey League (AHL) affiliate, the Bridgeport Sound Tigers, in late November.

The Islanders announced on January 15, 2013, that they had suspended Bailey due to sustaining an injury while playing for the Steelers, and that he would not collect any pay from the team during the suspension.

[17] During the 2017–18 season, Bailey scored his first career hat trick in a 6–4 loss to the Columbus Blue Jackets on December 14, 2017.

[18][19] Posting 18 goals and 53 assists for a career high 71 points, he was selected to his first NHL All-Star Game on January 10, 2018.

[26] In the off-season, on June 29, 2023, Bailey was traded to the Chicago Blackhawks along with a 2026 second-round draft pick for future considerations as the Islanders intended to dump his contract on a team with more space under the salary cap.

[27] Approximately two months later, on September 14, Bailey was signed to a professional tryout (PTO) agreement with the Ottawa Senators.

[29] On April 16, 2018, Bailey replaced Vince Dunn on Canada's senior team at the 2018 IIHF World Championship.